Synthesis of 4, 4', 6, 6'-Tetrasubstituted 2, 2'-Bi-1, 3, 5-triazines by the Ullmann Reaction of 4, 6-Disubstituted 2-Iodo-1, 3, 5-triazines

Abstract

4, 6-Bis(dimethylamino)-, 4, 6-bis(diphenylamino)- and 4, 6-diphenyl-2-iodo-1, 3, 5-triazines, [2 a], [2 b] and [2 c], were synthesized by the halogen exchange reaction of the corresponding chloro derivative with NaI. The yields of the reaction were good except for [2 a] which was prepared independently from cyanuric iodide and dimethylamine in satisfactory yield. The Ullmann reaction of [2 a]-[2c] with active copper powder gave the corresponding 4, 4', 6, 6'tetrasubstituted 2, 2'-bi-1, 3, 5-triazines [3a]-[3c] in 35, 45 and 20% yields, respectively. UV spectral data of [3a] and [3c] suggest that there may be no appreciable conjugative interaction between the two triazine rings.